Acetic Acid → 3-((4-Bromophenyl)sulfonyl)propanenitrile

Participants

Role	Name	HCID	Charge
Reactant	Acetic Acid	HCID 176	—
Reactant	Acrylonitrile	HCID 7855	—
Reactant	Sodium 4-bromobenzene-1-sulfinate--water (1/1/2)	HCID 23683129	—
Solvent	Water	HCID 962	—
Product	3-((4-Bromophenyl)sulfonyl)propanenitrile	HCID 2049781	86%

Reaction Conditions

Temperature	100 °C

Reaction Steps

To a suspension of sodium 4-bromophenylsulfinate dihydrate (130 g, 0.53 mol) in water (600 mL) was added acrylonitrile (70 mL, 1.07 mol) and acetic acid (62 mL, 1.07 mol). The reaction was stirred for 1.5 h at 100° C. then cooled to room temperature. The solid was filtered off, washed thoroughly with water and dried over P2O5 to give 3-[(4-bromophenyl)sulfonyl]propanenitrile (125 g). δH (400 MHz, CDCl3): 7.27–7.22 (4H, m), 2.85 (2H, t, J 7.6), 2.30 (2H, t, J 7.6).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07217740B2
Source dataset	uspto-grants-2007_05
ORD ID	ord-30054fec09ff41c79974f43873470f96
Source note	uspto-grants-2007_05